The Gorgeous Renaissance Village In Tuscany Famed For Cheese, Flowers, And Unique Landscapes

In the 15th century, a humble Tuscan town perched above the Val d'Orcia was transformed into the ideal Renaissance city under the direction of Pope Pius II, who grew up there, and then renamed Pienza. The innovative architecture and layout of the city, now classified as some of the earliest representations of Renaissance design, earned Pienza a UNESCO World Heritage Site designation in 1996. The town, with its grand palazzos, cathedrals, and winding streets, plus breathtaking views of the Tuscan countryside, is a worthy stop on an Italian road trip. In fact, according to Rick Steves, a road trip is the best way to explore this region of Tuscany. 

Besides its notable architecture, Pienza is also famed for its culinary and horticultural delights. The area is revered for its Pecorino di Pienza, an aged sheep's cheese local to the region. The city celebrates this bounty with a cheese fair annually in September and flower festival every May. The views from Pienza are as special as the town itself: The surrounding Val d'Orcia also became classified by UNESCO in 2004 for its distinctive and inspiring landscape. And the first Renaissance-style tiered "hanging gardens" were designed in Pienza at the Palazzo Piccolomini.

For foodies, one of the most unique times to visit Pienza is for the Fiera del Cacio (the Cheese Fair), when the town celebrates the famous cheese that has been produced there for centuries. The fair is typically held at the end of August. During the festival, cheese vendors set up stands in the main square for visitors to sample and purchase the famous pecorino. A unique highlight is the Cacio al Fuso competition, when locals roll cheese wheels towards a spindle to see who can get it closest. Live music and dancing add to the festive atmosphere. 

Another special festival in Pienza is Peinza e i fiori (Pienza and the Flowers), when the beautiful city is adorned with vibrant blooms to welcome in summer. The festival is usually held on the second weekend of May. During this time, visitors can see inside private Pienza buildings, courtyards, and gardens, which are decked out in gorgeous floral arrangements. However, even if you miss the festival, the fantastic garden of Palazzo Piccolomini boasts spectacular plantings to see year round. 

Pienza is an idyllic base from which to explore the surrounding Val d'Orcia. The glorious region is blessed with undulating hills studded with cypress trees, charming villages, and acres of vineyards. World-weary travelers have visited the valley for centuries because of Tuscany's many hidden hot springs, which were sought out for healing purposes and are still enjoyed today. Oenophiles will find much to discover in Tuscany, which is Italy's best region for wine, especially in the nearby wine-production towns of Montalcino and Montepulciano. And art and culture lovers will want to make a trip to learn more about the Renaissance in Florence, which is located a two-hour drive north of Pienza. Even movie buffs will be intrigued — the epic 2000 film "Gladiator" filmed scenes just outside Pienza. 

The best hotel to stay in Pienza is Hotel San Gregorio, voted as a Tripadvisor Travelers Choice Awards for 2024. The elegantly appointed 19 suites are centrally located for exploring the city by foot, and the hotel also boasts a pool and on-site Italian restaurant. Room rates here start at $161, at the time of writing, on average per night.